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{{Short description|Chemical compound}} |
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{{DISPLAYTITLE:''n''-Butanol}} |
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{{chembox |
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{{Chembox |
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|Verifiedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 396509157 |
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|verifiedrevid = 411004179 |
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| Name = ''n''-Butanol |
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| ImageFile = 1-Butanol skeletal.svg |
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|Name = 1-Butanol |
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| ImageName = 1-Butanol: skeletal structure |
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|ImageFileL1 = 1-Butanol skeletal.svg |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Butanol_flat_structure.png |
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|ImageNameL1 = Skeletal formula of n-butanol |
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| ImageName1 = 1-Butanol: flat structure |
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| ImageFile2 = Butan-1-ol-3D-vdW.png |
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|ImageFileR1 = Butan-1-ol-3D-vdW.png |
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|ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| ImageName2 = 1-Butanol: 3D space-filling structure |
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|ImageNameR1 = Spacefill model of n-butanol |
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| IUPACName = Butan-1-ol |
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|ImageFile2 = Butan-1-ol Lewis.svg |
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| OtherNames = 1-Butanol<br/>''n''-Butanol<br/>Butyl alcohol<br/>Butyl hydroxide<br/>Methylolpropane<br/>Propylcarbinol |
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|ImageFile2_Ref = {{chemboximage|correct|??}} |
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| Section1 = {{Chembox Identifiers |
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|ImageSize2 = 121 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|ImageName2 = Skeletal formula of n-butanol with all explicit hydrogens added |
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| UNII = 8PJ61P6TS3 |
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|PIN = Butan-1-ol<ref>{{Cite web|title = 1-Butanol - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=263&loc=ec_rcs|work = The PubChem Project|location = USA|publisher = National Center of Biotechnology Information}}</ref> |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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|OtherNames = ''n''-Butanol<br />''n''-Butyl alcohol<br />''n''-Butyl hydroxide<br />''n''-Propylcarbinol<br />''n''-Propylmethanol<br />1-Hydroxybutane<br />Methylolpropane |
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| ChEMBL = 14245 |
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|Section1 = {{Chembox Identifiers |
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| KEGG = D03200 |
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|CASNo = 71-36-3 |
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| InChI = 1/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|PubChem = 263 |
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| StdInChI = 1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 |
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|ChemSpiderID = 258 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = LRHPLDYGYMQRHN-UHFFFAOYSA-N |
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|UNII = 8PJ61P6TS3 |
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| CASNo = 71-36-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| EC-number = 200-751-6 |
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|EINECS = 200-751-6 |
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|UNNumber = 1120 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| ChemSpiderID = 258 |
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|DrugBank = DB02145 |
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| PubChem = 263 |
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|KEGG = D03200 |
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| RTECS = EO1400000 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| UNNumber = 1120 |
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|MeSHName = 1-Butanol |
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| SMILES = CCCCO |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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}} |
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|ChEBI = 28885 |
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| Section2 = {{Chembox Properties |
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|ChEMBL = 14245 |
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| Reference = <ref name="CRC">{{RubberBible62nd|page=C-191}}.</ref><ref name="ICSC">{{ICSC-ref|01|11|name=1-Butanol|date=April 2005}}.</ref><ref name="NIST">{{NIST chemistry|name=1-Butanol|id=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3|accessdate=2009-08-30}}.</ref><ref name="Counsell">{{citation | last1 = Counsell | first1 = J. F. | last2 = Hales | first2 = J. L. | last3 = Martin | first3 = J. F. | title = Thermodynamic properties of organic oxygen compounds. Part 16.—Butyl alcohol | journal = Trans. Faraday Soc. | year = 1965 | volume = 61 | pages = 1869–75 | doi = 10.1039/TF9656101869}}.</ref><ref>{{citation | last1 = Wilhoit | first1 = Randolph C. | last2 = Chao | first2 = Jing | last3 = Hall | first3 = Kenneth R. | title = Thermodynamic Properties of Key Organic Compounds in the Carbon Range C<sub>1</sub> to C<sub>4</sub>. Part 1. Properties of Condensed Phases | journal = J. Phys. Chem. Ref. Data | year = 1985 | volume = 14 | issue = 1 | pages = 1–175 | doi = 10.1063/1.555747}}.</ref> |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Formula = C<sub>4</sub>H<sub>10</sub>O |
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|RTECS = EO1400000 |
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| MolarMass = 74.122 g/mol |
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|Beilstein = 969148 |
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| Appearance = colourless liquid |
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|Gmelin = 25753 |
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| Density = 0.8098 g/cm<sup>3</sup> (20 °C) |
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|3DMet = B00907 |
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| Solubility = 7.7 g/100 mL (20 °C) |
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|SMILES = OCCCC |
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| MeltingPtC = −89.5 |
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|StdInChI = 1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 |
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| BoilingPtC = 117.7 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| TriplePt = −88.6 °C |
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|InChI = 1/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3 |
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| CriticalPt = 562±2 K, 45±4 bar |
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|StdInChIKey = LRHPLDYGYMQRHN-UHFFFAOYSA-N |
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| Viscosity = 3 ] (25 °C) |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Dipole = 1.52 ] |
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| RefractIndex = 1.399 (20 °C) |
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}} |
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| Section3 = {{Chembox Thermochemistry |
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| Reference = <ref name="NIST"/><ref name="Counsell"/> |
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| DeltaHf = −328±4 kJ/mol |
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| DeltaHc = −2670±20 kJ/mol |
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| Entropy = 225.7 J K<sup>−1</sup> mol<sup>−1</sup> |
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| HeatVapor = 51±5 kJ/mol |
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}} |
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| Section7 = {{Chembox Hazards |
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| Reference = <ref name="ICSC"/> |
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| ExternalMSDS = |
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| EUIndex = 603-004-00-6 |
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| EUClass = Harmful ('''Xn''') |
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| RPhrases = {{R10}}, {{R22}}, {{R37/38}}, {{R41}}, {{R67}} |
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| SPhrases = {{S2}}, {{S7/9}}, {{S13}}, {{S26}}, {{S37/39}}, {{S46}} |
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| NFPA-H = 1 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| FlashPt = 35 °C (95 °F) |
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| Autoignition = 345 °C (653 °F) |
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| ExploLimits = 1.4–11.3% |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunctn = ]<br/>]<br/>] |
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| Function = ]s |
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| OtherCpds = ]<br/>]<br/>] |
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|Section2 = {{Chembox Properties |
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|C=4 | H=10 | O=1 |
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|Appearance = Colourless, refractive liquid |
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|Odor = ]-like,<ref></ref> harsh, alcoholic and sweet |
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|Density = 0.81 g/cm<sup>3</sup> |
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|MeltingPtC = −89.8 |
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|BoilingPtC = 117.7 |
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|Solubility = 73 g/L at 25 °C |
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|SolubleOther = very soluble in ] <br /> miscible with ], ] |
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|LogP = 0.839 |
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|RefractIndex = 1.3993 (20 °C) |
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|Viscosity = 2.573 mPa·s (at 25 °C) <ref>{{cite journal | last1 = Dubey | first1 = Gyan | year = 2008 | title = Study of densities, viscosities, and speeds of sound of binary liquid mixtures of butan-1-ol with n-alkanes (C6, C8, and C10) at T = (298.15, 303.15, and 308.15) K | journal = The Journal of Chemical Thermodynamics | volume = 40 | issue = 2 | pages = 309–320 | doi = 10.1016/j.jct.2007.05.016 }}</ref> |
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|Dipole = 1.66 D |
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|pKa = 16.10 |
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|VaporPressure = 0.58 kPa (20 °C) ILO International Chemical Safety Cards (ICSC) |
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|MagSus = −56.536·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section3 = {{Chembox Thermochemistry |
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|DeltaHf = −328(4) kJ/mol |
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|DeltaHc = −2670(20) kJ/mol |
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|Entropy = 225.7 J/(K·mol) |
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}} |
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|Section4 = {{Chembox Hazards |
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|ExternalSDS = |
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|GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}} |
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|NFPA-H = 1 |
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|NFPA-F = 3 |
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|NFPA-R = 0 |
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|FlashPtC = 35 |
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|AutoignitionPtC = 343 |
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|ExploLimits = 1.45–11.25% |
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|LD50 = 790 mg/kg (rat, oral) |
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|PEL = TWA 100 ppm (300 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0076}}</ref> |
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|IDLH = 1400 ppm<ref name=PGCH/> |
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|REL = C 50 ppm (150 mg/m<sup>3</sup>) <ref name=PGCH/> |
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|LC50 = 9221 ppm (mammal)<br/>8000 ppm (rat, 4 ])<ref name=IDLH>{{IDLH|71363|N-butyl alcohol}}</ref> |
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|LDLo = 3484 mg/kg (rabbit, oral)<br/>790 mg/kg (rat, oral)<br/>1700 mg/kg (dog, oral)<ref name=IDLH/> |
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}} |
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|Section5 = {{Chembox Related |
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|OtherCompounds = ]<br/>]<br/>]<br/>] |
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}} |
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'''1-Butanol''', also known as '''butan-1-ol''' or '''''n''-butanol''', is a ] with the ] C<sub>4</sub>H<sub>9</sub>OH and a linear structure. ]s of 1-butanol are ], ] and ]. The unmodified term ] usually refers to the straight chain isomer. |
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1-Butanol occurs naturally as a minor product of the ] of ]s and other ]s<ref>{{citation | last1 = Hazelwood | first1 = Lucie A. | last2 = Daran | first2 = Jean-Marc | last3 = van Maris | first3 = Antonius J. A. | last4 = Pronk | first4 = Jack T. | last5 = Dickinson | first5 = J. Richard | title = The Ehrlich pathway for fusel alcohol production: a century of research on ''Saccharomyces cerevisiae'' metabolism | journal = Appl. Environ. Microbiol. | volume = 74 | issue = 8 | pages = 2259–66 | year = 2008 | pmid = 18281432 | pmc = 2293160 | doi = 10.1128/AEM.02625-07 | bibcode = 2008ApEnM..74.2259H }}.</ref> and is present in many foods and drinks.<ref name="EHC">{{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref><ref name="SIDS">{{SIDS-ref | name = ''n''-Butanol | id = 71363 | date = April 2005}}.</ref> It is also a permitted artificial flavorant in the United States,<ref>21 C.F.R. § 172.515; 42 FR 14491, Mar. 15, 1977, as amended.</ref> used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods, and cordials.<ref>{{citation | last1 = Hall | first1 = R. L. | last2 = Oser | first2 = B. L. | year = 1965 | title = Recent progress in the consideration of flavouring ingredients under the food additives amendment. III. Gras substances | journal = Food Technol. | page = 151}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> It is also used in a wide range of consumer products.<ref name="EHC"/> |
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'''''n''-Butanol''' or '''''n''-butyl alcohol''' or '''normal butanol''' is a primary ] with a 4-] structure and the ] C<sub>4</sub>H<sub>10</sub>O. Its ]s include ], ], and ]. Butanol is one of the group of "]s" (from the German for "bad liquor"), which have more than two carbon atoms and have significant solubility in water. |
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''n''-Butanol occurs naturally as a minor product of the ] of ]s and other ]s,<ref>{{citation | last1 = Hazelwood | first1 = Lucie A. | last2 = Daran | first2 = Jean-Marc | last3 = van Maris | first3 = Antonius J. A. | last4 = Pronk | first4 = Jack T. | last5 = Dickinson | first5 = J. Richard | title = The Ehrlich pathway for fusel alcohol production: a century of research on ''Saccharomyces cerevisiae'' metabolism | journal = Appl. Environ. Microbiol. | volume = 74 | issue = 8 | pages = 2259–66 | year = 2008 | pmid = 18281432 | pmc = 2293160 | doi = 10.1128/AEM.02625-07 | url = http://aem.asm.org/cgi/pmidlookup?view=long&pmid=18281432}}.</ref> and is present in many foods and beverages.<ref name="EHC">{{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref><ref name="SIDS">{{SIDS-ref | name = ''n''-Butanol | id = 71363 | date = April 2005}}.</ref> It is also a permitted artificial flavorant in the United States,<ref>21 C.F.R. § 172.515; 42 FR 14491, Mar. 15, 1977, as amended.</ref> used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods and cordials.<ref>{{citation | last1 = Hall | first1 = R. L. | last2 = Oser | first2 = B. L. | year = 1965 | title = Recent progress in the consideration of flavouring ingredients under the food additives amendement. III. Gras substances | journal = Food Technol. | page = 151}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> It is also used in a wide range of consumer products.<ref name="EHC"/> |
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The largest use of ''n''-butanol is as an industrial intermediate, particularly for the manufacture of ] (itself an artificial flavorant and industrial solvent). It is a ], manufactured from ] and usually used close to the point of manufacture. Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000 tonnes.<ref name="SIDS"/> |
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The largest use of 1-butanol is as an industrial intermediate, particularly for the manufacture of ] (itself an artificial flavorant and industrial solvent). It is a ] derived from ]. Estimated production figures for 1997 are: United States 784,000 tonnes; Western Europe 575,000 tonnes; Japan 225,000 tonnes.<ref name="SIDS"/> |
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==Production== |
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==Production== |
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''n''-Butanol is produced industrially from the petrochemical feedstock ]. Propylene is ] to ] (i.e. Oxo Process) in the presence of a ]-based ] similar to ]. The butyraldehyde is then ] to produce ''n''-butanol.<ref name="SIDS"/> |
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Since the 1950s, most 1-butanol is produced by the ] of ] (oxo process) to preferentially form the ] n-butanal. Typical catalysts are based on cobalt and rhodium. Butyraldehyde is then ] to produce butanol. |
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A second method for producing butanol involves the ] of propylene with CO and water:<ref name=Ull>{{Ullmann | first1 = Heinz-Dieter | last1 = Hahn | first2 = Georg | last2 = Dämbkes | first3 = Norbert | last3 = Rupprich | title = Butanols|doi = 10.1002/14356007.a04_463|year=2005}}.</ref> |
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==Industrial use== |
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:CH<sub>3</sub>CH=CH<sub>2</sub> + H<sub>2</sub>O + 2 CO → CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH + CO<sub>2</sub> |
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''n''-butanol is an intermediate in the production of ], ], ], ] and other butyl esters,<ref name="Mellan">{{citation | last = Mellan | first = I. | year = 1950 | title = Industrial Solvents | location = New York | publisher = Van Nostrand Reinhold | pages = 482–88}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref><ref name="Doolittle">{{citation | last = Doolittle | first = A. K. | year = 1954 | title = The Technology of Solvents and Plasticizers | location = New York | publisher = Wiley | pages = 644–45}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> butyl ethers such as ], ] and ] and the corresponding butyl ether acetates. Other industrial uses include the manufacture of pharmaceuticals, polymers, ] plastics, herbicide esters (e.g., ], ])<ref name="Monich">{{citation | last = Monich | first = J. A. | year = 1968 | title = Alcohols: Their Chemistry, Properties, and Manufacture | location = New York | publisher = Chapman and Reinhold}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> and ]. It is also used as a diluent/reactant in the manufacture of ]–] and ]–formaldehyde resins.<ref name="SIDS"/> |
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In former times, butanol was prepared from ], which can be obtained from ]. |
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==Other uses== |
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''n''-Butanol is used as an ingredient in perfumes and as a solvent for the extraction of ]s.<ref name="Mellan"/> ''n''-Butanol is also used as an extractant in the manufacture of ]s, ]s, and ]s;<ref name="Mellan"/><ref name="Doolittle"/> a solvent for paints, coatings, natural resins, gums, synthetic resins, dyes, ]s, and ].<ref name="Mellan"/><ref name="Doolittle"/> Other miscellaneous applications of ''n''-butanol are as a swelling agent in textiles, as a component of ]s, cleaning formulations, ]s, and repellents;<ref name="EHC"/> and as a component of ore floation agents,<ref name="Monich"/> and of wood-treating systems.<ref>{{citation | inventor1-last = Amundsen | inventor1-first = J. | inventor2-last = Goodwin | inventor2-first = R. J. | inventor3-last = Wetzel | inventor3-first = W. H. | assignee = Reichhold Chemicals Inc. | year = 1979 | title = Water-soluble pentachlorophenol and tetrachlorophenol wood-treating systems | country-code = ZA | patent-number = 7801031 | publication-date = 28 Feb. 1979}}.</ref> |
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Butanol can also be produced by ] of ] by bacteria. Prior to the 1950s, '']'' was used in ] to produce butanol. Research in the past few decades showed results of other microorganisms that can produce butanol through fermentation. |
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''n''-Butanol has been proposed as a substitute for ] and ]. It is produced in small quantities in nearly all ]s (see ]), but species of ] produce much higher yields of butanol, and research is currently underway to increase the ultimate yield of biobutanol from biomass. |
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Butanol can be produced via furan hydrogenation over Pd or Pt catalyst at high temperature and high pressure.https://pubs.rsc.org/en/content/articlehtml/2014/gc/c3gc41183d |
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The production or, in some cases, use of the following substances may result in exposure to ''n''-butanol: ], ]s, rubber cement, dyes, fruit essences, lacquers, motion picture and photographic films, raincoats, perfumes, ] plastics, ], safety glass, ] varnish, and waterproofed cloth.<ref name="EHC"/> |
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==Industrial use== |
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===Occurrence in Nature=== |
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Constituting 85% of its use, 1-butanol is mainly used in the production of ]es. It is a popular solvent, e.g. for ]. A variety of butanol derivatives are used as solvents, e.g. ] or ]. Many ]s are based on butyl esters, e.g., ]. The ] ] is used to produce polymers. It is the precursor to ]s.<ref name=Ull/> |
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]s emitted by the ] of ]s contain n-butanol. |
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===Biofuel=== |
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==Occurrence in food== |
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1-Butanol has been proposed as a substitute for ] and ]. It is produced in small quantities in nearly all ] (see ]). ] produces much higher yields of butanol. Research is underway to increase the biobutanol yield from ]. |
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''n''-Butanol occurs naturally as a result of carbohydrate fermentation in a number of alcoholic beverages, including beer,<ref>{{citation | last = Bonte | first = W. | year = 1979 | title = Congener substances in German and foreign beers | journal = Blutalkohol | volume = 16 | pages = 108–24}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> grape brandies,<ref>{{citation | last1 = Schreier | first1 = Peter | last2 = Drawert | first2 = Friedrich | last3 = Winkler | first3 = Friedrich | year = 1979 | title = Composition of neutral volatile constituents in grape brandies | journal = J. Agric. Food Chem. | volume = 27 | issue = 2 | pages = 365–72| doi = 10.1021/jf60222a031}}.</ref> wine,<ref>{{citation | last = Bonte | first = W. | year = 1978 | title = Congener content of wine and similar beverages | journal = Blutalkohol | volume = 15 | pages = 392–404}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> and whisky.<ref>{{citation | last1 = Postel | first1 = W. | last2 = Adam | first2 = L. | year = 1978 | title = Gas chromatographic characterization of whiskey. III. Irish whiskey | journal = Branntweinwirtschaft | volume = 118 | pages = 404–7}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> It has been detected in the volatiles of hops,<ref>{{citation | last1 = Tressl | first1 = Roland | last2 = Friese | first2 = Lothar | last3 = Fendesack | first3 = Friedrich | last4 = Koeppler | first4 = Hans | year = 1978 | title = Studies of the volatile composition of hops during storage | journal = J. Agric. Food Chem. | volume = 26 | issue = 6 | pages = 1426–30 | doi = 10.1021/jf60220a036}}.</ref> jack fruit,<ref>{{citation | last1 = Swords | first1 = G. | last2 = Bobbio | first2 = P. A. | last3 = Hunter | first3 = G. L. K. | year = 1978 | title = Volatile constituents of jack fruit (''Arthocarpus heterophyllus'') | journal = J. Food Sci. | volume = 43 | issue = 2 | pages = 639–40 | doi = 10.1111/j.1365-2621.1978.tb02375.x}}.</ref> heat-treated milks,<ref>{{citation | last1 = Jaddou | first1 = Haytham A. | last2 = Pavey | first2 = John A. | last3 = Manning | first3 = Donald J. | year = 1978 | title = Chemical analysis of flavor volatiles in heat-treated milks | journal = J. Dairy Res. | volume = 45 | issue = 3 | pages = 391–403 | doi = 10.1017/S0022029900016617}}.</ref> musk melon,<ref>{{citation | last1 = Yabumoto | first1 = K. | last2 = Yamaguchi | first2 = M. | last3 = Jennings | first3 = W. G. | year = 1978 | title = Production of volatile compounds by Muskmelon, ''Cucumis melo'' | journal = Food Chem. | volume = 3 | issue = 1 | pages = 7–16 | doi = 10.1016/0308-8146(78)90042-0}}.</ref> cheese,<ref>{{citation | last1 = Dumont | first1 = Jean Pierre | last2 = Adda | first2 = Jacques | year = 1978 | title = Occurrence of sesquiterpones in mountain cheese volatiles | journal = J. Agric. Food Chem. | volume = 26 | issue = 2 | pages = 364–67 | doi = 10.1021/jf60216a037}}.</ref> southern pea seed,<ref>{{citation | last1 = Fisher | first1 = Gordon S. | last2 = Legendre | first2 = Michael G. | last3 = Lovgren | first3 = Norman V. | last4 = Schuller | first4 = Walter H. | last5 = Wells | first5 = John A. | year = 1979 | title = Volatile constituents of southernpea seed | journal = J. Agric. Food Chem. | volume = 27 | issue = 1 | pages = 7–11 | doi = 10.1021/jf60221a040}}.</ref> and cooked rice.<ref>{{citation | last1 = Yajima | first1 = Izumi | last2 = Yanai | first2 = Tetsuya | last3 = Nakamura | first3 = Mikio | last4 = Sakakibara | first4 = Hidemasa | last5 = Habu | first5 = Tsutomu | year = 1978 | title = Volatile flavor components of cooked rice | journal = Agric. Biol. Chem. | volume = 42 | issue = 6 | pages = 1229–33 | url = http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=bbb1961&cdvol=42&noissue=6&startpage=1229&lang=en&from=jnlabstract}}.</ref> ''n''-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein.<ref>{{citation | unused_data = DUPLICATE DATA: journal = 55 | last1 = Chang | first1 = S. S. | last2 = Peterson | first2 = K. J. | last3 = Ho | first3 = C. | year = 1978 | title = Chemical reactions involved in the deep-fat frying of foods | journal = J. Am. Oil Chem. Soc. | pages = 718–27}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> |
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Butanol is considered as a potential ] (]). Butanol at 85 percent strength can be used in cars designed for gasoline without any change to the engine (unlike 85% ethanol), and it provides more energy for a given volume than ethanol, almost as much as gasoline. Therefore, a vehicle using butanol would return fuel consumption more comparable to gasoline than ethanol. Butanol can also be added to diesel fuel to reduce soot emissions.<ref>{{cite journal|author=Antoni, D.|author2=Zverlov, V.|author3=Schwarz, W. H.|name-list-style=amp|year=2007|title=Biofuels from Microbes|journal=Applied Microbiology and Biotechnology|volume=77|issue=1|pages=23–35|doi=10.1007/s00253-007-1163-x|pmid=17891391|s2cid=35454212}}</ref> |
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''n''-Butanol is used as an ingredient in processed and artificial flavourings,<ref name="Mellan"/> and for the extraction lipid-free protein from egg yolk,<ref>{{citation | last1 = Meslar | first1 = Harry W. | last2 = White | first2 = Harold B., III | year = 1978 | title = Preparation of lipid-free protein extracts of egg yolk | journal = Anal. Biochem. | volume = 91 | issue = 1 | pages = 75–81 | doi = 10.1016/0003-2697(78)90817-5 | pmid = 9762085}}.</ref> natural flavouring materials and vegetable oils, the manufacture of hop extract for beermaking, and as a solvent in removing pigments from moist curd ].<ref>{{citation | last1 = Bray | first1 = Walter J. | last2 = Humphries | first2 = Catherine | year = 1978 | title = Solvent fractionation of leaf juice to prepare green and white protein products | journal = J. Sci. Food Agric. | volume = 29 | issue = 10 | pages = 839–46 | doi = 10.1002/jsfa.2740291003}}.</ref> |
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The production of, or in some cases, the use of, the following substances may result in exposure to 1-butanol: ], ]s, ], dyes, fruit essences, lacquers, motion picture, and photographic films, raincoats, perfumes, ] plastics, ], safety glass, ] varnish, and waterproofed cloth.<ref name="EHC"/> |
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==Metabolism and toxicity== |
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''n''-Butanol is readily absorbed through the intestinal tract and lungs, and also to some extent through the skin.<ref>{{citation | last1 = Theorell | first1 = Hugo | last2 = Bonnichsen | first2 = Roger | year = 1951 | title = Studies on Liver Alcohol Dehydrogenase I. Equilibria and Initial Reaction Velocities | journal = Acta. Chem. Scand. | volume = 5 | pages = 1105–26 | doi = 10.3891/acta.chem.scand.05-1105 | url = http://actachemscand.dk/pdf/acta_vol_05_p1105-1126.pdf | last3 = Holtermann | first3 = Hugo | last4 = Sörensen | first4 = JöRgine Stene | last5 = Sörensen | first5 = Nils Andreas}}. {{citation | last = Winer | first = Alfred D. | year = 1958 | title = A Note of the Substrate Specificity of Horse Liver Alcohol Dehydrogenase | journal = Acta. Chem. Scand. | volume = 12 | pages = 1695–96 | doi = 10.3891/acta.chem.scand.12-1695 | url = http://actachemscand.dk/pdf/acta_vol_12_p1695-1696.pdf | last2 = Nurmikko | first2 = V. | last3 = Hartiala | first3 = K. | last4 = Hartiala | first4 = K. | last5 = Veige | first5 = S. | last6 = Diczfalusy | first6 = E.}}. {{citation | last1 = Merritt | first1 = A. Donald | last2 = Tomkins | first2 = Gordon M. | year = 1959 | title = Reversible Oxidation of Cyclic Secondary Alcohols by Liver Alcohol Degydrogenase | journal = J. Biol. Chem. | volume = 234 | issue = 10 | pages = 2778–82 | url = http://www.jbc.org/cgi/reprint/234/10/2778}}. {{citation | last1 = von Wartburg | first1 = Jean-Pierre | last2 = Bethane | first2 = J. L. | last3 = Vallee | first3 = B. L. | year = 1964 | title = Human Liver Alcohol Dehydrogenase: Kinetic and Physiochemical Properties | journal = Biochemistry | volume = 3 | issue = 11 | pages = 1775–82 | doi = 10.1021/bi00899a033}}.</ref> It is metabolized completely in vertebrates in a manner similar to ]: ] coverts ''n''-butanol to ]; this is then converted to ] by ]. Butyric acid can be fully metabolized to ] and ] by the ] pathway, of which it is naturally the penultimate step. In the rat, only 0.03% of an oral dose of 2000 mg/kg was excreted in the urine.<ref>{{citation | last1 = Gaillard | first1 = D. | last2 = Derache | first2 = R. | year = 1965 | title = Métabilisation de différents alcools présents dans les biossons alcooliques chez le rat | journal = Trav. Soc. Pharmacol. Montpellier | volume = 25 | pages = 541–62}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> |
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==Occurrence in nature== |
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The acute toxicity of ''n''-butanol is relatively low, with oral ] values of 2290–4360 mg/kg (rat; comparable values for ethanol are 7000–15000 mg/kg).<ref name="SIDS"/><ref>{{SIDS-ref|name=Ethanol|id=64175|date=August 2005}}.</ref> No deaths were reported at an inhaled concentration of 8000 ppm (4-hour exposure, rats). At sub-lethal doses, ''n''-butanol acts as a ] of the ], similar to ethanol: one study in rats indicated that the intoxicating potency of ''n''-butanol is some six times higher than that of ethanol, possibly because of its slower transformation by alcohol dehydrogenase.<ref>{{citation | last1 = McCreery | first1 = N. J. | last2 = Hunt | first2 = W. A. | year = 1978 | title = Physico-chemical correlates of alcohol intoxication | journal = Neuropharmacology | volume = 17 | issue = 7 | pages = 451–61 | doi = 10.1016/0028-3908(78)90050-3 | pmid = 567755}}.</ref> |
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Butan-1-ol occurs naturally as a result of carbohydrate fermentation in a number of alcoholic beverages, including beer,<ref>{{citation | last = Bonte | first = W. | year = 1979 | title = Congener substances in German and foreign beers | journal = Blutalkohol | volume = 16 | pages = 108–24}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> grape brandies,<ref>{{citation | last1 = Schreier | first1 = Peter | last2 = Drawert | first2 = Friedrich | last3 = Winkler | first3 = Friedrich | year = 1979 | title = Composition of neutral volatile constituents in grape brandies | journal = J. Agric. Food Chem. | volume = 27 | issue = 2 | pages = 365–72| doi = 10.1021/jf60222a031}}.</ref> wine,<ref>{{citation | last = Bonte | first = W. | year = 1978 | title = Congener content of wine and similar beverages | journal = Blutalkohol | volume = 15 | pages = 392–404}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> and whisky.<ref>{{citation | last1 = Postel | first1 = W. | last2 = Adam | first2 = L. | year = 1978 | title = Gas chromatographic characterization of whiskey. III. Irish whiskey | journal = Branntweinwirtschaft | volume = 118 | pages = 404–7}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> It has been detected in the volatiles of hops,<ref>{{citation | last1 = Tressl | first1 = Roland | last2 = Friese | first2 = Lothar | last3 = Fendesack | first3 = Friedrich | last4 = Koeppler | first4 = Hans | year = 1978 | title = Studies of the volatile composition of hops during storage | journal = J. Agric. Food Chem. | volume = 26 | issue = 6 | pages = 1426–30 | doi = 10.1021/jf60220a036}}.</ref> jack fruit,<ref>{{citation | last1 = Swords | first1 = G. | last2 = Bobbio | first2 = P. A. | last3 = Hunter | first3 = G. L. K. | year = 1978 | title = Volatile constituents of jack fruit (''Arthocarpus heterophyllus'') | journal = J. Food Sci. | volume = 43 | issue = 2 | pages = 639–40 | doi = 10.1111/j.1365-2621.1978.tb02375.x}}.</ref> heat-treated milks,<ref>{{citation | last1 = Jaddou | first1 = Haytham A. | last2 = Pavey | first2 = John A. | last3 = Manning | first3 = Donald J. | year = 1978 | title = Chemical analysis of flavor volatiles in heat-treated milks | journal = J. Dairy Res. | volume = 45 | issue = 3 | pages = 391–403 | doi = 10.1017/S0022029900016617| s2cid = 85985458 }}.</ref> musk melon,<ref>{{citation | last1 = Yabumoto | first1 = K. | last2 = Yamaguchi | first2 = M. | last3 = Jennings | first3 = W. G. | year = 1978 | title = Production of volatile compounds by Muskmelon, ''Cucumis melo'' | journal = Food Chem. | volume = 3 | issue = 1 | pages = 7–16 | doi = 10.1016/0308-8146(78)90042-0}}.</ref> cheese,<ref>{{citation | last1 = Dumont | first1 = Jean Pierre | last2 = Adda | first2 = Jacques | year = 1978 | title = Occurrence of sesquiterpones in mountain cheese volatiles | journal = J. Agric. Food Chem. | volume = 26 | issue = 2 | pages = 364–67 | doi = 10.1021/jf60216a037}}.</ref> southern pea seed,<ref>{{citation | last1 = Fisher | first1 = Gordon S. | last2 = Legendre | first2 = Michael G. | last3 = Lovgren | first3 = Norman V. | last4 = Schuller | first4 = Walter H. | last5 = Wells | first5 = John A. | year = 1979 | title = Volatile constituents of southernpea seed | journal = J. Agric. Food Chem. | volume = 27 | issue = 1 | pages = 7–11 | doi = 10.1021/jf60221a040}}.</ref> and cooked rice.<ref>{{citation | last1 = Yajima | first1 = Izumi | last2 = Yanai | first2 = Tetsuya | last3 = Nakamura | first3 = Mikio | last4 = Sakakibara | first4 = Hidemasa | last5 = Habu | first5 = Tsutomu | year = 1978 | title = Volatile flavor components of cooked rice | journal = Agric. Biol. Chem. | volume = 42 | issue = 6 | pages = 1229–33 | url = https://www.jstage.jst.go.jp/article/bbb1961/42/6/42_6_1229/_pdf/-char/en | doi = 10.1271/bbb1961.42.1229 | doi-access = free }}.</ref> 1-Butanol is also formed during deep frying of corn oil, cottonseed oil, trilinolein, and triolein.<ref>{{citation | last1 = Chang | first1 = S. S. | last2 = Peterson | first2 = K. J. | last3 = Ho | first3 = C. | year = 1978 | title = Chemical reactions involved in the deep-fat frying of foods | journal = J. Am. Oil Chem. Soc. | volume = 55 | issue = 10 | pages = 718–27| doi = 10.1007/BF02665369 | pmid = 730972 | s2cid = 97273264 }}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> |
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''n''-Butanol is a natural component of many alcoholic beverages, albeit in low (but variable) concentrations.<ref>{{citation | last = Woo | first = Kang-Lyung | title = Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography | journal = J. AOAC Int. | year = 2005 | volume = 88 | issue = 5 | pages = 1419–27 | pmid = 16385992 | doi = 10.5555/jaoi.2005.88.5.1419}}.</ref><ref>{{citation | last1 = Lachenmeier | first1 = Dirk W. | last2 = Haupt | first2 = Simone | last3 = Schulz | first3 = Katja | title = Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products | journal = Regulat. Toxicol. Pharmacol. | year = 2008 | volume = 50 | issue = 3 | pages = 313–21 | pmid = 18295386 | doi = 10.1016/j.yrtph.2007.12.008}}.</ref> It (along with similar ]s) is reputed to be responsible for severe "]s", although experiments in animal models show no evidence for this.<ref>{{citation | last1 = Hori | first1 = Hisako | last2 = Fujii | first2 = Wataru | last3 = Hatanaka | first3 = Yutaka | last4 = Suwa | first4 = Yoshihide | title = Effects of fusel oil on animal hangover models | journal = Alcohol Clin. Exp. Res. | year = 2003 | volume = 27 | issue = 8 Suppl | pages = 37S–41S | pmid = 12960505 | doi = 10.1097/01.ALC.0000078828.49740.48}}.</ref> ''n''-Butanol has occasionally been abused by ]s, leading to a range of adverse health effects.<ref>{{citation | last1 = McKee | first1 = Martin | last2 = Sűzcs | first2 = Sándor | last3 = Sárváry | first3 = Attila | last4 = Adany | first4 = Roza | last5 = Kiryanov | first5 = Nikolay | last6 = Saburova | first6 = Ludmilla | last7 = Tomkins | first7 = Susannah | last8 = Andreev | first8 = Evgeny | last9 = Leon | first9 = David A. | title = The composition of surrogate alcohols consumed in Russia | journal = Alcohol. Clin. Exp. Res. | year = 2005 | volume = 29 | issue = 10 | pages = 1884–88 | pmid = 16269919 | doi = 10.1097/01.alc.0000183012.93303.90}}.</ref><ref>{{citation | last1 = Bunc | first1 = M. | last2 = Pezdir | first2 = T. | last3 = Možina | first3 = H. | last4 = Možina | first4 = M. | last5 = Brvar | first5 = M. | title = Butanol ingestion in an airport hangar | journal = Hum. Exp. Toxicol. | year = 2006 | volume = 25 | issue = 4 | pages = 195–97 | pmid = 16696295 | doi = 10.1191/0960327106ht607oa}}.</ref> |
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Butan-1-ol is one of the "]s" (from the German for "bad liquor"), which include alcohols that have more than two carbon atoms and have significant solubility in water.<ref>{{Cite journal |last1=Atsumi |first1=S. |last2=Hanai |first2=T. |last3=Liao |first3=J. C. |year=2008 |title=Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels |journal=Nature |volume=451 |issue=7174 |pages=86–89 |doi=10.1038/nature06450 |pmid=18172501|bibcode=2008Natur.451...86A |s2cid=4413113 }}</ref> It is a natural component of many alcoholic beverages, albeit in low and variable concentrations.<ref>{{citation |last=Woo |first=Kang-Lyung |title=Determination of low molecular weight alcohols including fusel oil in various samples by diethyl ether extraction and capillary gas chromatography |journal=J. AOAC Int. |year=2005 |volume=88 |issue=5 |pages=1419–27 |doi=10.1093/jaoac/88.5.1419 |pmid=16385992 |doi-access=free}}.</ref><ref>{{citation |last1=Lachenmeier |first1=Dirk W. |last2=Haupt |first2=Simone |last3=Schulz |first3=Katja |title=Defining maximum levels of higher alcohols in alcoholic beverages and surrogate alcohol products |journal=] |year=2008 |volume=50 |issue=3 |pages=313–21 |pmid=18295386 |doi=10.1016/j.yrtph.2007.12.008}}.</ref> It (along with similar fusel alcohols) is reputed to be responsible for severe ]s, although experiments in animal models show no evidence for this.<ref>{{citation |last1=Hori |first1=Hisako |last2=Fujii |first2=Wataru |last3=Hatanaka |first3=Yutaka |last4=Suwa |first4=Yoshihide |title=Effects of fusel oil on animal hangover models |journal=Alcohol. Clin. Exp. Res. |year=2003 |volume=27 |issue=8 Suppl |pages=37S–41S |pmid=12960505 |doi=10.1097/01.ALC.0000078828.49740.48|doi-access=free }}.</ref> |
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1-Butanol is used as an ingredient in processed and artificial flavorings,<ref name="Mellan">{{citation | last = Mellan | first = I. | year = 1950 | title = Industrial Solvents | location = New York | publisher = Van Nostrand Reinhold | pages = 482–88}}, cited in {{EHC-ref | id = 65 | name = Butanols: four isomers | date = 1987 | isbn = 92-4-154265-9}}.</ref> and for the extraction of lipid-free protein from egg yolk,<ref>{{citation | last1 = Meslar | first1 = Harry W. | last2 = White | first2 = Harold B. III | year = 1978 | title = Preparation of lipid-free protein extracts of egg yolk | journal = Anal. Biochem. | volume = 91 | issue = 1 | pages = 75–81 | doi = 10.1016/0003-2697(78)90817-5 | pmid = 9762085}}.</ref> natural flavouring materials and vegetable oils, the manufacture of hop extract for beermaking, and as a solvent in removing pigments from moist curd ].<ref>{{citation | last1 = Bray | first1 = Walter J. | last2 = Humphries | first2 = Catherine | year = 1978 | title = Solvent fractionation of leaf juice to prepare green and white protein products | journal = J. Sci. Food Agric. | volume = 29 | issue = 10 | pages = 839–46 | doi = 10.1002/jsfa.2740291003| bibcode = 1978JSFA...29..839B }}.</ref> |
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==Other hazards== |
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Liquid ''n''-butanol, as is common with most organic solvents, is extremely irritating to the eyes; repeated contact with the skin can also cause irritation.<ref name="SIDS"/> This is believed to be a generic effect of "defatting". No skin sensitization has been observed. Irritation of the respiratory pathways occurs only at very high concentrations (>2400 ppm).<ref name="Monell">{{citation | last1 = Wysocki | first1 = C. J. | last2 = Dalton | first2 = P. | year = 1996 | title = Odor and Irritation Thresholds for 1-Butanol in Humans | publisher = Monell Chemical Senses Center | location = Philadelphia}}, cited in {{SIDS-ref | name = ''n''-Butanol | id = 71363 | date = April 2005}}.</ref> |
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==Metabolism and toxicity== |
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With a ] of 29 °C (84 °F),<ref name="ICSC"/> ''n''-butanol presents a moderate fire hazard: it is slightly more flammable than ] or ] but less flammable than many other common organic solvents. The depressant effect on the central nervous system (similar to ethanol intoxication) is a potential hazard when working with ''n''-butanol in enclosed spaces, although the odour threshold (0.2–30 ppm) is far below the concentration which would have any neurological effect.<ref name="Monell"/><ref>{{citation | last1 = Cometto-Muñiz | first1 = J. Enrique | last2 = Cain | first2 = William S. | year = 1998 | title = Trigeminal and Olfactory Sensitivity: Comparison of Modalities and Methods of Measurement | journal = Int. Arch. Occup. Environ. Health | volume = 71 | issue = 2 | pages = 105–10 | doi = 10.1007/s004200050256 | pmid = 9580447}}.</ref> |
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The acute toxicity of 1-butanol is relatively low, with oral ] values of 790–4,360 mg/kg (rat; comparable values for ethanol are 7,000–15,000 mg/kg).<ref name="SIDS"/><ref>{{SIDS-ref|name=Ethanol|id=64175|date=August 2005}}.</ref><ref name=Ull/> It is metabolized completely in vertebrates in a manner similar to ]: ] converts 1-butanol to ]; this is then converted to ] by ]. Butyric acid can be fully metabolized to ] and ] by the ] pathway. In the rat, only 0.03% of an oral dose of 2,000 mg/kg was excreted in the urine.<ref>{{citation |last1=Gaillard |first1=D. |last2=Derache |first2=R. |year=1965 |title=Métabilisation de différents alcools présents dans les biossons alcooliques chez le rat |journal=Trav. Soc. Pharmacol. Montpellier |volume=25 |pages=541–62}}, cited in {{EHC-ref |id=65 |name=Butanols: four isomers |date=1987 |isbn=92-4-154265-9}}.</ref> At sub-lethal doses, 1-butanol acts as a ] of the ], similar to ethanol: one study in rats indicated that the intoxicating potency of 1-butanol is about 6 times higher than that of ethanol, possibly because of its slower transformation by alcohol dehydrogenase.<ref>{{citation |last1=McCreery |first1=N. J. |last2=Hunt |first2=W. A. |year=1978 |title=Physico-chemical correlates of alcohol intoxication |journal=Neuropharmacology |volume=17 |issue=7 |pages=451–61 |doi=10.1016/0028-3908(78)90050-3 |pmid=567755|s2cid=19914287 }}.</ref> |
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===Other hazards=== |
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''n''-Butanol is of low toxicity to aquatic vertebrates and invertebrates. It is rapidly biodegraded in water, although an estimated 83% partitions to air where it is degraded by ]s with a half-life of 1.2–2.3 days. It has low potential to ].<ref name="SIDS"/> A potential hazard of significant discharges to watercourses is the rise in ] (C.O.D.) associated with its biodegradation. |
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Liquid 1-butanol, as is common with most organic solvents, is extremely irritating to the eyes; repeated contact with the skin can also cause irritation.<ref name="SIDS"/> This is believed to be a generic effect of ]. No skin sensitization has been observed. Irritation of the respiratory pathways occurs only at very high concentrations (>2,400 ppm).<ref name="Monell">{{citation |last1=Wysocki |first1=C. J. |last2=Dalton |first2=P. |year=1996 |title=Odor and Irritation Thresholds for 1-Butanol in Humans |publisher=Monell Chemical Senses Center |location=Philadelphia}}, cited in {{SIDS-ref |name=''n''-Butanol |id=71363 |date=April 2005}}.</ref> |
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With a ] of 35 °C, 1-butanol presents a moderate fire hazard: it is slightly more flammable than ] or ] but less flammable than many other common organic solvents. The depressant effect on the central nervous system (similar to ethanol intoxication) is a potential hazard when working with 1-butanol in enclosed spaces, although the odour threshold (0.2–30 ppm) is far below the concentration which would have any neurological effect.<ref name="Monell"/><ref>{{citation |last1=Cometto-Muñiz |first1=J. Enrique |last2=Cain |first2=William S. |year=1998 |title=Trigeminal and Olfactory Sensitivity: Comparison of Modalities and Methods of Measurement |journal=Int. Arch. Occup. Environ. Health |volume=71 |issue=2 |pages=105–10 |doi=10.1007/s004200050256 |pmid=9580447 |bibcode=1998IAOEH..71..105C |s2cid=25246408 |url=http://www.escholarship.org/uc/item/52f8x48p }}.</ref> |
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==See also== |
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* ] |
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==External links== |
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==External links== |
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*{{SIDS|name=''n''-Butanol|id=71363|date=April 2005}} |
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*{{SIDS|name=''n''-Butanol|id=71363|date=April 2005}} |
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*{{EHC|65|name=Butanols: four isomers}} |
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*{{EHC|65|name=Butanols: four isomers}} |
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*{{HSG|id=003|number=3|name=1-Butanol|date=1987|isbn=92-4-154365-6}} |
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*{{HSG|id=003|number=3|name=1-Butanol|date=1987|issn=0259-7268}} <!-- The ISBN printed in the document is bad; it causes a checksum error --> |
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==References== |
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==References== |
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{{reflist|2}} |
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{{Reflist|2}} |
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{{Alcohols}} |
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{{Alcohols}} |
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{{Sedatives}} |
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{{GABAAR PAMs}} |
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{{Authority control}} |
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{{DEFAULTSORT:Butanol, n-}} |
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{{DEFAULTSORT:Butanol, 1-}} |
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